CAS Number24390-14-5
SynonymsDoxycycline Hyclate / Monohydrate; DOXYCYCLINE HYCLATE USP GRADE; Azudoxat; Tetradox; HYDRAMYCIN; DOXYCYCLINE HYDRATE; Doxycycline Hyclate; Doxycycline hydrochloride hemiethanolate hemihydrate; Ronaxan; DOXYCYCLINE MONOHYDRATE; Doxycycline hyclate COS; Doxycycline Hyclate USP; Mespafin; Retens; Doxycycline API; Doxycycline Hydrochlocide; Doxycycline Hc1; Doxycycline HCl
Molecular FormulaC22H24N2O8.1/2C2H6O.ClH.1/2H2O
Molecular Weight512.94
Purity≥93.5 (HPLC)%
Boiling Point685.2ºC at 760 mmHg
Melting Point206-209?C (dec.)
Appearancepowder
Symbol
Signal WordWarning
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| Chemical & Physical Properties | |
|---|---|
| CAS Number | 24390-14-5 |
| Catalog No. | 2A-9010246 |
| Chinese Name | 盐酸强力霉素 |
| Synonyms | Doxycycline Hyclate / Monohydrate; DOXYCYCLINE HYCLATE USP GRADE; Azudoxat; Tetradox; HYDRAMYCIN; DOXYCYCLINE HYDRATE; Doxycycline Hyclate; Doxycycline hydrochloride hemiethanolate hemihydrate; Ronaxan; DOXYCYCLINE MONOHYDRATE; Doxycycline hyclate COS; Doxycycline Hyclate USP; Mespafin; Retens; Doxycycline API; Doxycycline Hydrochlocide; Doxycycline Hc1; Doxycycline HCl |
| Molecular Formula | C22H24N2O8.1/2C2H6O.ClH.1/2H2O |
| Molecular Weight | 512.94 |
| Purity | ≥93.5 (HPLC) |
| Boiling Point | 685.2ºC at 760 mmHg |
| Melting Point | 206-209?C (dec.) |
| Appearance | powder |
| Storage Condition | 2~8°C |
| Application | Doxycycline hyclate is a tetracycline antibiotic and broad-spectrum metalloproteinase (MMP) inhibitor. |
| HTC | 2941302000 |
| PubChem ID | 57654124 |
| MDL Number | MFCD07357237 |
| SMILES | Cl[H].Cl[H].[H]O[H].CCO.C[C@@H]1C2[C@H](O)C3[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]3(O)C(O)=C2C(=O)c4c(O)cccc14.C[C@@H]5C6[C@H](O)C7[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]7(O)C(O)=C6C(=O)c8c(O)cccc58 |
| InChI | 1S/2C22H24N2O8.C2H6O.2ClH.H2O/c2*1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)17(27)14-15(24(2)3)18(28)13(21(23)31)20(30)22(14,32)19(12)29;1-2-3;;;/h2*4-7,10,14-15,17,25,27-29,32H,1-3H3,(H2,23,31);3H,2H2,1H3;2*1H;1H2/t2*7-,10?,14?,15-,17-,22-;;;;/m00..../s1 |
| InChI Key | HALQELOKLVRWRI-ZVACAFRPSA-N |
| Beilstein/REAXYS | 5702728 |
| NACRES Code | NA.85 |
| UNSPSC | 51284027 |
| Hazard Symbols | Transport |
| MSDS | msds/10246_1_24390_14_5.pdf |
| Bioactivity | Doxycycline (hyclate) is a tetracycline antibiotic and broad-spectrum metalloproteinase (MMP) inhibitor. Related Catalog Signaling Pathways >> Metabolic Enzyme/Protease >> MMP Research Areas >> Infection In Vitro Doxycycline shows excellent effectiveness and time-dependent characteristics against M. gallisepticum strain S6 in vitro[2]. Osteoblasts exposed to the composite containing 25 μg/mL doxycycline (DOX)/β-cyclodextrin (βCD) has increased cell proliferation (p < 0.05) compared to control osteoblast cultures at all experimental time points, reaching a maximum in the second week. Alkaline phosphatase (AP) activity and collagen secretion levels are also elevated in osteoblasts exposed to the DOX/βCD composite (p < 0.05 vs. controls) and reach a maximum after 14 days[3]. Doxycycline (20 nM) inhibits ECM (extracellular matrix) production and remodeling in both SMC (smooth muscle cell) types of cultures, and synthesis of collagens and isoprenylated proteins in SMC-Ch (a cholesterol-rich diet) is a higher than in SMC-C (a standard diet)[4]. In Vivo In heterozygous (HT) Col3a1 knockout mice, after 3 months of treatment with doxycycline or placebo, 9-month-old HT or wild-type (WT) mice are subjected to surgical stressing of the aorta. A 3-fold increase in stress-induced aortic lesions found in untreated HT mice 1 week after intervention (cumulative score 4.5±0.87 versus 1.3±0.34 in WT, p<0.001) is fully prevented in the doxycycline (25 or 100 mg/kg, p.o.)-treated group (1.1±0.56)[1]. Kinase Assay Gelatin (0.1% (w/v) is added to standard LaemmLi acrylamide polymerization mixture. Tissue extract is mixed 1:2 with sample buffer [250 mM Tris-Cl pH 6.8, 10% (w/v) SDS, 20% (v/v) glycerol, 0.005% (w/v) bromphenol blue]. Serum is diluted 1:10 with electrophoresis buffer (2.5 mM Tris, 20 mM glycine, 0.005% SDS) and mixed 1:2 with sample buffer. Twenty μLs are loaded after 10-min incubation at room temperature without boiling. After electrophoresis at 90 V, the gels are soaked in 2.5% (w/v) Triton X-100, incubated 2 to 3 days at 37°C in gelatin digestion buffer [50 mM Tris-Cl, pH 8.0, 8 mM CaCl2, 10 mM ZnSO2, 0.02% (w/v) NaN3], stained in 0.05% Coomassie blue R-250 in acetic acid/methanol/water (1:4.5:4.5 by volume), destained in 10% acetic acid and 5% methanol, and scanned for lysis band intensity. The lysis band intensity is proportional to gelatinase activity and is quantified densitometrically by using One-Dimensional Scan software. The result, a number between 0.07 and 3.75, is normalized to the protein content by dividing the densitometry result with the relative optical density from the BCA protein assay kit result. The result is used for the analysis as the arbitrary unit. For the total MMP activity results of lysis bands of pro-MMP-9, active MMP-9, pro-MMP-2, and active MMP-2 are added. A protein size marker is used to determine the correct size. Cell Assay All in vitro treatments are performed in SMC cultures at 90% confluence, when ECM synthesis in SMC starts to be evident. Doxycycline (20 nM) is diluted in culture medium at a concentration of 10 μg/mL (20 nM), at which no toxicity or variation in primary cultured SMC proliferation has been reported, as well as in other cell lines and the incubation time is 48 h. SMC-C and SMC-Ch are seeded at equal cell density in 6-well plates and, when confluence reaches 90%, 1 mL culture medium is added to each well containing 3.7×104 Bq L-[5-3H]-proline (9.62×1011 Bq/mmol). After 48 h incubation, cells are lysed with 0.5 mL 0.5 mol/L NaOH for 1 h. The resulting solution is neutralized with an equal amount of 0.5 mol/L HCl, and 50 μL are used to measure total proteins with the Bradford method. One volume of 10% TCA is added to the remaining 250 μL and centrifuged at 13,000 g for 15 min at 4°C. The resulting precipitate is dissolved in 100 μL 0.2 mol/L NaOH, and then neutralized with 1 mol/L HCl. The solution is incubated with collagenase buffer (Tris-HCl, pH 7.6 20 mM, and CaCl2 250 mM final concentration) and 10 units of collagenase at 37°C overnight. Then, 150 μL 10% TCA are added and centrifuged at 13000 g for 15 min at 4°C. The resulting supernatant is added to 4 mL of scintillation fluid and the radioactivity is measured in a liquid scintillation counter LS 600 TA. Animal Admin Two groups of 6-month-old female heterozygous (HT) Col3a1 knockout mice are treated for 3 months with doxycycline. Treatment is provided with food containing 200 or 800 mg/kg of doxycycline. Because preliminary measured food intake of these mice is averaged at 3.5 g/day and the average body weight of animals is 25 g, the average drug dose for low- and high-dose groups is 25 (Doxy25) or 100 (Doxy100) mg/kg per day, respectively. Untreated (wild type) WT and HT mice are maintained on a regular diet (NIH-07 mouse/rat diet) and served as controls. After 3 months, under general inhalation anesthesia (2% of isoflurane in oxygen) and aseptic conditions, the abdominal aortas are surgically exposed and stressed by the following technique: the blood flow is stopped by occluding the abdominal aorta against the spinal column with a sterile cotton-tip applicator pressed at the level of the renal arteries. After 30 s a second applicator is pressed at the level of iliac bifurcation and the first applicator is abruptly released, followed by release of the second applicator. The abdominal incision is sutured closed, and mice are returned to home cages. The treatment is continued after the intervention. One week after intervention mice are euthanized by an overdose of isoflurane. Blood is collected, and aortas and segments of colon and skin are harvested. References [1]. Wilfried Briest, et al. Doxycycline ameliorates the susceptibility to aortic lesions in a mouse model for the vascular type of Ehlers-Danlos syndrome. J Pharmacol Exp Ther. 2011 Jun;337(3):621-7. [2]. Zhang N, et al. The PK/PD Interactions of Doxycycline against Mycoplasma gallisepticum. Front Microbiol. 2016 May 4;7:653. [3]. Trajano VC, et al. Osteogenic activity of cyclodextrin-encapsulated doxycycline in a calcium phosphate PCL and PLGA composite. Mater Sci Eng C Mater Biol Appl. 2016 Jul 1;64:370-5. [4]. Palomino-Morales R, et al. Inhibition of extracellular matrix production and remodeling by doxycycline in smooth muscle cells. J Pharmacol Sci. 2016 Mar 25. Epub ahead of print [5]. Wang X, et al. FTO is required for myogenesis by positively regulating mTOR-PGC-1α pathway-mediated mitochondria biogenesis. Cell Death Dis. 2017 Mar 23;8(3):e2702. Chemical & Physical Properties Boiling Point 685.2ºC at 760 mmHg Melting Point 206-209?C (dec.) Molecular Formula C22H24N2O8.1/2C2H6O.ClH.1/2H2O Molecular Weight 512.94 Flash Point 368.2ºC PSA 392.70000 LogP 2.24370 Vapour Pressure 1.03E-19mmHg at 25°C InChIKey RBXVTKJNXYJLNQ-FSKLHFAESA-N SMILES CC1c2cccc(O)c2C(O)=C2C(=O)C3(O)C(O)=C(C(N)=O)C(=O)C(N(C)C)C3C(O)C21.CC1c2cccc(O)c2C(O)=C2C(=O)C3(O)C(O)=C(C(N)=O)C(=O)C(N(C)C)C3C(O)C21.CCO.Cl Storage condition 2~8°C |
| Use of | Doxycycline (hyclate) is a tetracycline antibiotic and broad-spectrum metalloproteinase (MMP) inhibitor. Properties Articles157 Name doxycycline hyclate Synonym More Synonyms Doxycycline hyclate Biological Activity Description Doxycycline (hyclate) is a tetracycline antibiotic and broad-spectrum metalloproteinase (MMP) inhibitor. Related Catalog Signaling Pathways >> Metabolic Enzyme/Protease >> MMP Research Areas >> Infection In Vitro Doxycycline shows excellent effectiveness and time-dependent characteristics against M. gallisepticum strain S6 in vitro[2]. Osteoblasts exposed to the composite containing 25 μg/mL doxycycline (DOX)/β-cyclodextrin (βCD) has increased cell proliferation (p < 0.05) compared to control osteoblast cultures at all experimental time points, reaching a maximum in the second week. Alkaline phosphatase (AP) activity and collagen secretion levels are also elevated in osteoblasts exposed to the DOX/βCD composite (p < 0.05 vs. controls) and reach a maximum after 14 days[3]. Doxycycline (20 nM) inhibits ECM (extracellular matrix) production and remodeling in both SMC (smooth muscle cell) types of cultures, and synthesis of collagens and isoprenylated proteins in SMC-Ch (a cholesterol-rich diet) is a higher than in SMC-C (a standard diet)[4]. References [1]. Wilfried Briest, et al. Doxycycline ameliorates the susceptibility to aortic lesions in a mouse model for the vascular type of Ehlers-Danlos syndrome. J Pharmacol Exp Ther. 2011 Jun;337(3):621-7. [2]. Zhang N, et al. The PK/PD Interactions of Doxycycline against Mycoplasma gallisepticum. Front Microbiol. 2016 May 4;7:653. [3]. Trajano VC, et al. Osteogenic activity of cyclodextrin-encapsulated doxycycline in a calcium phosphate PCL and PLGA composite. Mater Sci Eng C Mater Biol Appl. 2016 Jul 1;64:370-5. [4]. Palomino-Morales R, et al. Inhibition of extracellular matrix production and remodeling by doxycycline in smooth muscle cells. J Pharmacol Sci. 2016 Mar 25. Epub ahead of print [5]. Wang X, et al. FTO is required for myogenesis by positively regulating mTOR-PGC-1α pathway-mediated mitochondria biogenesis. Cell Death Dis. 2017 Mar 23;8(3):e2702. Chemical & Physical Properties PSA 392.70000 LogP 2.24370 InChIKey RBXVTKJNXYJLNQ-FSKLHFAESA-N |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available |
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